Acetonitrile → HCID 18973023, compound

HRID 2394362Notes

Reaction equation

HRID 2394362 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12](=[O:19])[C:13]3[S:17][CH:16]=[C:15]([CH3:18])[CH:14]=3)[C:7](=[O:11])[NH:8]2)=[N:4][CH:3]=1.[C:20](=[O:26])=[N:21]S(Cl)(=O)=O.C(#N)C.ClS(NC=O)(=O)=O>CS(C)=O.C(O)(=O)C.O>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12](=[O:19])[C:13]3[S:17][CH:16]=[C:15]([CH3:18])[CH:14]=3)[C:7](=[O:11])[N:8]2[C:20]([NH2:21])=[O:26])=[N:4][CH:3]=1

Participants

8

Reactant 4

HCID 6342AcetonitrileHCID 70918Chlorosulfonyl isocyanateHCID 15228322HCID 15228322, compoundHCID 18973047HCID 18973047, compound2×

Product 1

HCID 18973023HCID 18973023, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The title compound was prepared from 6-fluoro-3-(4-methyl-2-thenoyl)-4-azaoxindole (Example 36) according to the procedure of Example 2C, using 6-fluoro-3-(4-methyl-2-thenoyl)-4-azaoxindole (614 mg, 2.22 mmol), N-chlorosulfonyl isocyanate (0.30 mL, 3.45 mmol) and acetonitrile (10 mL). The crude N-chlorosulfonyl carboxamide was hydrolysed by stirring in DMSO (4 mL) overnight in a flask open to the air. The product was isolated by dilution with water, filtration, and recrystallization from acetic acid. Yield: 249 mg (35%). M.p.>250°.

Sources & evidence

ORD record
ord-1ff3a87778ae4d3e904295bf0219b8f4
Source dataset
uspto-grants-1998_09
Patent number
US05811432

Reaction notes

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